EP3261455A1 - Allulosesirup - Google Patents

Allulosesirup

Info

Publication number
EP3261455A1
EP3261455A1 EP16708198.3A EP16708198A EP3261455A1 EP 3261455 A1 EP3261455 A1 EP 3261455A1 EP 16708198 A EP16708198 A EP 16708198A EP 3261455 A1 EP3261455 A1 EP 3261455A1
Authority
EP
European Patent Office
Prior art keywords
allulose
syrup
allulose syrup
weight
dry solids
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP16708198.3A
Other languages
English (en)
French (fr)
Other versions
EP3261455B8 (de
EP3261455B1 (de
Inventor
Ryan D. WOODYER
Peter Lloyd-Jones
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tate and Lyle Technology Ltd
Tate and Lyle Solutions USA LLC
Original Assignee
Tate and Lyle Technology Ltd
Tate and Lyle Ingredients Americas LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=55456836&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP3261455(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Tate and Lyle Technology Ltd, Tate and Lyle Ingredients Americas LLC filed Critical Tate and Lyle Technology Ltd
Priority to EP22150616.5A priority Critical patent/EP4042873B1/de
Publication of EP3261455A1 publication Critical patent/EP3261455A1/de
Application granted granted Critical
Publication of EP3261455B1 publication Critical patent/EP3261455B1/de
Publication of EP3261455B8 publication Critical patent/EP3261455B8/de
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/15—Vitamins
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K13/00—Sugars not otherwise provided for in this class
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00—Function of food ingredients
    • A23V2200/02—Antioxidant
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00—Function of food ingredients
    • A23V2200/20—Ingredients acting on or related to the structure
    • A23V2200/212—Buffering agent
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/60—Sugars, e.g. mono-, di-, tri-, tetra-saccharides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the present invention relates to allulose syrups, use of allulose syrups in the manufacture of food or beverage products, and food and beverage products made using the allulose syrups.
  • nutritive sweeteners such as sucrose (generally referred to as 'sugar' or 'table sugar'), glucose, fructose, corn syrup, high fructose corn syrup and the like.
  • sucrose generally referred to as 'sugar' or 'table sugar'
  • glucose fructose
  • corn syrup high fructose corn syrup and the like.
  • excess intake of nutritive sweeteners, such as sucrose has long been associated with an increase in diet-related health issues, such as obesity, heart disease, metabolic disorders and dental problems. This worrying trend has caused consumers to become increasingly aware of the importance of adopting a healthier lifestyle and reducing the level of nutritive sweeteners in their diet.
  • Allulose also known as D- psicose. Allulose is known as a "rare sugar", since it occurs in nature in only very small amounts. It provides around 70% of the sweetness of sucrose, but only around 5% of the calories (approximately 0.2 kcal/g). It may therefore essentially be considered to be a 'zero calorie' sweetener.
  • 201 1/0275138 discloses a ketose 3-epimerase derived from a microorganism of the Rhizobium genus.
  • This protein shows a high specificity to D- or L- ketopentose and D- or L-ketohexose, and especially to D-fructose and D-psicose.
  • This document also discloses a process for producing ketoses by using the protein.
  • Korean patent no. 100832339 discloses a Sinorhizobium YB-58 strain which is capable of converting fructose into psicose (i.e. allulose), and a method of producing psicose using a fungus body of the Sinorhizobium YB-58 strain.
  • Korean patent application no. 1020090098938 discloses a method of producing psicose using E. coli wherein the E. coli expresses a polynucleotide encoding a psicose 3- epimerase.
  • Allulose is present in processed cane and beet molasses, steam treated coffee, wheat plant products and high fructose corn syrup.
  • D-allulose is the C-3 epimer of D-fructose and the structural differences between allulose and fructose result in allulose not being metabolized by the human body to any significant extent, and thus having "zero" calories.
  • allulose is thought to be a promising candidate as a replacement for nutritive sweeteners and as a sweet bulking agent, as it has essentially no calories and is reported to be sweet while maintaining similar properties to sucrose.
  • allulose syrup i.e. a syrup comprising allulose and water. It has been found that allulose syrups may be susceptible to degradation over time (i.e. gradual reduction in allulose content), to color formation, to the formation of impurities (such as hydroxymethylfurfural - HMF), to crystallization, and to inadequate microbial stability.
  • An object of the present invention is to provide an allulose syrup that addresses the above problems.
  • the present invention provides an allulose syrup having a total dry solids content of from 50% to 80% by weight, and comprising allulose in an amount of at least 80% by weight on a dry solids basis, wherein the pH of the syrup is from 2.5 to 6.0.
  • the allulose syrup has a total dry solids content of from 50% to 70% by weight, and comprises allulose in an amount of at least 80% by weight on a dry solids basis, wherein the pH of the syrup is from 2.5 to 6.0.
  • the allulose syrup has a total dry solids content of from 70% to 80% by weight, and comprises allulose in an amount of at least 90% by weight on a dry solids basis, wherein the pH of the syrup is from 3.0 to 5.0.
  • the total dry solids content of the allulose syrup is from 71 % to 78% by weight. In another embodiment, the total dry solids content of the allulose syrup is from 71 % to 73% by weight. In another embodiment, the total dry solids content of the allulose syrup is from 76% to 78% by weight. In another embodiment, the total dry solids content of the allulose syrup is from 50% to 71 % by weight.
  • the pH of the allulose syrup is from 3.5 to 4.5. In an embodiment, the pH of the allulose syrup is from 3.8 to 4.2.
  • the allulose syrup comprises allulose in an amount of at least 95% by weight on a dry solids basis. In an embodiment, the allulose syrup comprises less than 1000 ppm of HMF. In an embodiment, the allulose syrup comprises sulfur dioxide in an amount of from 0.1 to 20 ppm.
  • the allulose syrup comprises sulfur dioxide in an amount of from 1 to 20 ppm.
  • the allulose syrup comprises less than 10 parts per billion of isovaleraldehyde. In an embodiment, the allulose syrup comprises less than 2 parts per billion of 2- aminoacetophenone.
  • the allulose syrup further comprises one or more additives.
  • the one or more additives may include a stability-enhancing additive.
  • the one or more additives may include an anti-oxidant.
  • the one or more additives may include a buffer.
  • the one or more additive may be selected from the group consisting of ascorbic acid or salts thereof; isoascorbic acid (erythorbate) or salts thereof; citric acid or salts thereof; acetic acid or salts thereof; salts of bisulfite or metabisulfite; and tocopherol acetate.
  • the shelf-life of the allulose syrup as defined by maintaining an allulose content of greater than 80% by weight on a dry solids basis is at least 3, 6, 9, 12 months, or more than 12 months.
  • an allulose content of greater than 80% by weight on a dry solids basis is maintained when the allulose syrup is stored for at least 3, 6, 9, 12 months, or more than 12 months.
  • the shelf-life of the allulose syrup as defined by maintaining an allulose content of greater than 90% by weight on a dry solids basis is at least 3, 6, 9, 12 months, or more than 12 months. In an embodiment, the shelf-life of the allulose syrup as defined by maintaining an allulose content of greater than 95% by weight on a dry solids basis is at least 3, 6, 9, 12 months, or more than 12 months.
  • the present invention provides a process for preparing an allulose syrup according to the first aspect. The process for preparing the allulose syrup includes:
  • the process includes:
  • the process includes:
  • the dry solids content is from 70 to 78% by weight
  • the allulose content of the syrup is at least 90% by weight on a dry solids basis
  • the pH is controlled to between 3.5 to 4.5.
  • the present invention provides the use of the allulose syrup according to the first aspect in the preparation of a food or beverage product.
  • the present invention provides a food or beverage product comprising an allulose syrup according to the first aspect and at least one additional food or beverage ingredient.
  • the at least one additional food or beverage ingredient includes at least one ingredient selected from the group consisting of flavorants, colorants, sweeteners other than allulose, dietary fibers, acidulants, water, and combinations thereof.
  • the allulose syrup comprises 50 to 80% dry solids by weight, and greater than 80% allulose on a dry solids basis, a measured pH between 2.5 and 6.0 and a shelf life of at least 3 months.
  • the allulose syrup comprises 60 to 80% dry solids by weight, and greater than 90% allulose on a dry solids basis, a measured pH between 3.0 and 5.0 and a shelf life of at least 3 months.
  • the allulose syrup comprises 70 to 80% dry solids by weight, and greater than 90% allulose on a dry solids basis, a measured pH between 3.0 and 5.0 and a shelf life of at least 3 months.
  • Figure 1 shows how the purity of an allulose syrup composition (initial pH 3.4) changes over time at 25 °C, 30 °C and 35 °C.
  • Figure 2 shows how the color of an allulose syrup composition (initial pH 3.4) changes over time at 25 °C, 30 °C and 35 °C.
  • Figure 3 shows how the amount of HMF in an allulose syrup composition (initial pH 3.4) changes over time at 25 °C, 30 °C and 35 °C.
  • Figure 4 shows how the pH of an allulose syrup composition (initial pH 3.4) changes over time at 25 °C, 30 °C and 35 °C. It should be noted that the data points for storage at 25 °C are the same as for storage at 30 °C.
  • Figure 5 shows how the pH of an allulose syrup composition (initial pH 4.0) changes over time at 4 °C, 25 °C, 35 °C and 50 °C.
  • Figure 6 shows how the color of an allulose syrup composition (initial pH 4.0) changes over time at 4 °C, 25 °C, 35 °C and 50 °C.
  • Figure 7 shows how the amount of HMF in an allulose syrup composition (initial pH 4.0) changes over time at 4 °C, 25 °C, 35 °C and 50 °C.
  • Figure 8 shows how the purity of an allulose syrup composition (initial pH 4.0) changes over time at 4 °C, 25 °C and 35 °C.
  • Figure 9 shows how the pH of the allulose syrup product samples of Example 2 changes over time at 40 °C.
  • Figure 10 shows how the pH of the allulose syrup product samples of Example 2 changes over time at 50 °C.
  • Figure 1 1 compares change in the pH of the allulose syrup product samples of Example 2 (starting pH 4.0) at 50 °C with an allulose syrup composition with an initial pH of 3.9.
  • Figure 12 shows how the allulose purity of the allulose syrup product samples of Example 2 changes over time at 40 °C.
  • Figure 13 shows how the allulose purity of the allulose syrup product samples of Example 2 changes over time at 50 °C.
  • Figure 14 shows how the color of the allulose syrup product samples of Example 2 changes over time at 40 °C.
  • Figure 15 shows how the color of the allulose syrup product samples of Example 2 changes over time at 50 °C.
  • Figure 16 shows how the HMF content of the allulose syrup product samples of Example 2 changes over time at 40 °C.
  • Figure 17 shows how the HMF content of the allulose syrup product samples of Example 2 changes over time at 50 °C.
  • Figure 18 shows how the allulose content of the allulose syrup product samples of Example 5 changes over time at different temperature, pH and DS content.
  • Figure 19 shows how the allulose content of the allulose syrup product samples of Example 5 changes over time at 25 °C.
  • Figure 20 shows how the allulose content of the allulose syrup product samples of Example 5 changes over time at 35 °C.
  • Figure 21 shows how the HMF content of the allulose syrup product samples of Example 5 changes over time at 25 °C.
  • Figure 22 shows how the HMF content of the allulose syrup product samples of Example 5 changes over time at 35 °C.
  • Figure 23 shows how the color of the allulose syrup product samples of Example 5 changes over time at 25 °C.
  • Figure 24 shows how the color of the allulose syrup product samples of Example 5 changes over time at 35 °C.
  • Figure 25 shows how the pH of the allulose syrup product samples of Example 6 over time is affected by additives.
  • Figure 26 shows how the allulose purity of the allulose syrup product samples of Example 6 over time is affected by additives.
  • Figure 27 shows how the allulose purity of the allulose syrup product samples of Example 6 over time is affected by the addition of ascorbate and isoascorbate.
  • Figure 28 shows how the allulose purity of the allulose syrup product samples of Example 6 over time is affected by the addition of citrate and acetate.
  • Figure 29 shows how the HMF content of the allulose syrup product samples of Example 6 over time is affected by the addition of ascorbate and isoascorbate.
  • Figure 30 shows the change in allulose content at 6 months at 77% DS as modelled using DOE software according to Example 7 (each contour line represents a 2% decrease in change in allulose content from time 0).
  • Figure 31 shows the change in allulose content at 6 months at 25 °C as modelled using DOE software according to Example 7.
  • Figure 32 shows color change at 6 months at 77% DS as modelled using DOE software according to Example 7.
  • Figure 33 shows color change at 6 months at 25 °C as modelled using DOE software according to Example 7.
  • Figure 34 shows HMF formation at 6 months and 77% DS as modelled using DOE software according to Example 7.
  • the present invention is based on the finding that allulose syrups with improved storage stability can be prepared by careful control of certain parameters.
  • allulose refers to a monosaccharide sugar of the structure shown as a Fischer projection in below Formula I. It is also known as "D-psicose”:
  • the present invention provides an allulose syrup having a total dry solids content of from 50% to 80% by weight, and comprising allulose in an amount of at least 80% by weight on a dry solids basis, wherein the pH of the syrup is from 2.5 to 6.0.
  • the allulose syrup has a total dry solids content of from 70% to 80% by weight, and comprises allulose in an amount of at least 90% by weight on a dry solids basis, wherein the pH of the syrup is from 3.0 to 5.0.
  • the total dry solids content of the allulose syrup is from 50% to 80% by weight.
  • the total dry solids content may be 50%, 51 %, 52%, 53%, 54%, 55%, 56%, 57%, 58%, 59%, 60%, 61 %, 62%, 63%, 64%, 65%, 66%, 67%, 68%, 69%, 70%, 71 %, 72%, 73%, 74%, 75%, 76%, 77%, 78%, 79% or 80% by weight, as well as all intermediate values.
  • the total dry solids content of the allulose syrup is from 70% to 80% by weight.
  • the total dry solids content may be 70%, 71 %, 72%, 73%, 74%, 75%, 76%, 77%, 78%, 79% or 80% by weight, as well as all intermediate values.
  • the total dry solids content of the allulose syrup is from 71 % to 78% by weight.
  • the total dry solids content of the allulose syrup is from 71 % to 73% by weight.
  • the total dry solids content of the allulose syrup is from 76% to 78% by weight.
  • the total dry solids content of the allulose syrup is from 50% to 70% by weight.
  • compositional stability of the allulose syrup is generally highest towards the lower end of the total dry solids content range of the invention
  • microbial stability is generally highest towards the higher end of the total dry solids content range of the invention. Accordingly, the selection of a suitable total dry solids content within the range of the invention can be made depending on the key attribute for the particular application.
  • the pH of the allulose syrup is from 2.5 to 6.0.
  • the pH of the syrup may be 2.5, 2.6, 2.7, 2.8, 2.9, 3.0, 3.1 , 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4.0, 4.1 , 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 5.0, 5.1 , 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, 5.8, 5.9 or 6.0, as well as all intermediate values.
  • the pH of the allulose syrup is from 3.0 to 5.0.
  • the pH of the syrup may be 3.0, 3.1 , 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4.0, 4.1 , 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9 or 5.0 as well as all intermediate values.
  • the pH of the allulose syrup is from 3.5 to 4.5.
  • the pH of the syrup may be 3.5, 3.6, 3.7, 3.8, 3.9, 4.0, 4.1 , 4.2, 4.3, 4.4 or 4.5 as well as all intermediate values.
  • the pH of the allulose syrup is from 3.8 to 4.2.
  • the pH of the allulose syrup is about 4.0.
  • the allulose syrup comprises allulose in an amount of at least 80% by weight on a dry solids basis (i.e., of the total dry solids present in the allulose syrup, at least 80% by weight is allulose).
  • the allulose syrup may comprise allulose in an amount of 80%, 81 %, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91 %, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99% or 100% by weight on a dry solids basis, as well as all intermediate values.
  • the allulose syrup comprises allulose in an amount of at least 90% by weight on a dry solids basis (i.e., of the total dry solids present in the allulose syrup, at least 90% by weight is allulose).
  • the allulose syrup may comprise allulose in an amount of 90%, 91 %, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99% or 100% by weight on a dry solids basis, as well as all intermediate values.
  • the allulose syrup comprises allulose in an amount of at least 95% by weight on a dry solids basis.
  • the allulose syrup comprises less than 1000 ppm of HMF (hydroxymethylfurfural).
  • the allulose syrup may comprise less than 900 ppm, less than 800 ppm, less than 700 ppm, less than 600 ppm, less than 500 ppm, less than 400 ppm, less than 300 ppm, less than 200 ppm or less than 100 ppm of HMF.
  • the allulose syrup comprises more than 0.1 ppm and less than 1000 ppm of HMF (hydroxymethylfurfural), for example more than 0.1 ppm and less than 900 ppm, more than 0.1 ppm and less than 800 ppm, more than 0.1 ppm and less than 700 ppm, more than 0.1 ppm and less than 600 ppm, more than 0.1 ppm and less than 500 ppm, more than 0.1 ppm and less than 400 ppm, more than 0.1 ppm and less than 300 ppm, more than 0.1 ppm and less than 200 ppm, or more than 0.1 ppm and less than 100 ppm.
  • HMF hydroxymethylfurfural
  • the allulose syrup comprises sulfur dioxide in an amount of from 0.1 to 20 ppm.
  • the allulose syrup comprises sulfur dioxide in an amount of from 1 to 20 ppm.
  • the allulose syrup comprises less than 10 parts per billion of isovaleraldehyde. In an embodiment, the allulose syrup comprises less than 2 parts per billion of 2- aminoacetophenone.
  • the allulose syrup further comprises one or more additives.
  • the one or more additives may include a stability-enhancing additive.
  • the one or more additives may include an anti-oxidant.
  • the one or more additives may include a buffer. The incorporation of a buffer in the allulose syrup maintains the pH of the allulose within the desired range for a longer period of time, such that storage stability is further enhanced.
  • the stability enhancing additives are included at around 0.01 -2.0% by weight based on the total weight of the allulose syrup.
  • the stability-enhancing additive may be selected from the group consisting of ascorbic acid and salts thereof; isoascorbic acid (erythorbate) and salts thereof; citric acid and salts thereof; acetic acid and salts thereof; and salts of bisulfite and metabisulfite; and tocopherol acetate.
  • suitable salts include alkali metal salts, particularly sodium and potassium salts, and especially sodium salts.
  • Specific examples of stability-enhancing additives useful in the present invention include ascorbate, isoascorbate, sodium citrate, sodium acetate, tocopherol acetate and metabisulfite.
  • the stability enhancing additives are included at around 0.2% by weight based on the total weight of the allulose syrup in the case of ascorbic acid or salts thereof; isoascorbic acid (erythorbate) or salts thereof; citric acid or salts thereof; acetic acid or salts thereof; and tocopherol acetate. In an embodiment, the stability enhancing additives are included at around 0.02% by weight based on the total weight of the allulose syrup in the case of salts of bisulfite or metabisulfite. The concentration of buffer included in the allulose syrup may be around 0.01-2.0% by weight based on the total weight of the allulose syrup.
  • the concentration of buffer included in the allulose syrup may be around 0.2% by weight based on the total weight of the allulose syrup in the case of ascorbic acid or salts thereof; isoascorbic acid (erythorbate) or salts thereof; citric acid or salts thereof; acetic acid or salts thereof; and tocopherol acetate.
  • the concentration of buffer included in the allulose syrup may be around 0.02% by weight based on the total weight of the allulose syrup in the case of salts of bisulfite or metabisulfite.
  • the allulose syrup of the present invention has a shelf-life of at least 3 months.
  • the allulose syrup of the present invention maintains an allulose content of at least 80% on a dry solids basis for at least 3 months, preferably at least 6 months, at least 9 months, at least 12 months or more than 12 months.
  • the allulose syrup of the present invention has a shelf-life of at least 3 months.
  • the allulose syrup of the present invention maintains an allulose content of at least 90% on a dry solids basis for at least 3 months, preferably at least 6 months, at least 9 months, at least 12 months or more than 12 months.
  • the allulose syrup of the present invention preferably has a shelf-life of at least 6 months.
  • the allulose syrup of the present invention preferably maintains an allulose content of at least 95% on a dry solids basis for at least 6 months, preferably at least 9 months, at least 12 months or more than 12 months. Allulose content is measured by standard HPLC methods such as the Sacch.03 method set forth by the corn refiners association (http://corn.org/wp-content uploads/2009/12/SACCH.03.pdf).
  • the syrup has a limited amount of the following compounds: less than 1000 ppm hydroxymethylfurfural (HMF); sulphur dioxide at a concentration of less than 20 parts per million; isovaleraldehyde at a measured concentration of less than 10 parts per billion; and 2- aminoacetophenone at a concentration of less than 2 parts per billion.
  • HMF hydroxymethylfurfural
  • sulphur dioxide at a concentration of less than 20 parts per million
  • isovaleraldehyde at a measured concentration of less than 10 parts per billion
  • 2- aminoacetophenone at a concentration of less than 2 parts per billion.
  • the syrup can have any of the following compounds alone or in combination thereof: a stability enhancing ingredient including one or more of: 1 ) ascorbic acid or salts thereof, 2) isoascorbic acid (erythorbate) or salts thereof, 3) citric acid or salts thereof, 4) acetic acid or salts thereof, 5) salts of bisulfite or metabisulfite, and/or 6) tocopherol acetate.
  • a stability enhancing ingredient including one or more of: 1 ) ascorbic acid or salts thereof, 2) isoascorbic acid (erythorbate) or salts thereof, 3) citric acid or salts thereof, 4) acetic acid or salts thereof, 5) salts of bisulfite or metabisulfite, and/or 6) tocopherol acetate.
  • the allulose syrup may have a concentration of greater than 90% (e.g. greater than 95%) with a shelf-life of at least 3, 6, 9, 12 months, or more than 12 months.
  • the present invention provides a process for preparing an allulose syrup.
  • the process comprises: providing an allulose syrup; adjusting the dry solids content of the allulose syrup such that it is from 50% to 80% by weight; adjusting the allulose content of the allulose syrup such that allulose is present in an amount of at least 80% by weight on a dry solids basis; and controlling the pH of the allulose syrup so that it is from 2.5 to 6.0.
  • the process for preparing an allulose syrup comprises: providing an allulose syrup; adjusting the dry solids content of the allulose syrup such that it is from 60% to 80% by weight; adjusting the allulose content of the allulose syrup such that allulose is present in an amount of at least 80% by weight on a dry solids basis; and controlling the pH of the allulose syrup so that it is from 2.5 to 6.0.
  • the process for preparing an allulose syrup comprises: providing an allulose syrup; adjusting the dry solids content of the allulose syrup such that it is from 70% to 80% by weight; adjusting the allulose content of the allulose syrup such that allulose is present in an amount of at least 90% by weight on a dry solids basis; and controlling the pH of the allulose syrup so that it is from 3.0 to 5.0.
  • the process for preparing an allulose syrup comprises: providing an allulose syrup; adjusting the dry solids content of the allulose syrup such that it is from 70% to 78% by weight; adjusting the allulose content of the allulose syrup such that allulose is present in an amount of at least 90% by weight on a dry solids basis; and controlling the pH of the allulose syrup so that it is from 3.5 to 4.5.
  • the process optionally comprises removing or avoiding the production of HMF to limit the content to less than 1000 ppm, or more preferably less than 100 ppm.
  • the process optionally comprises removing or avoiding the production of isovaleraldehyde to limit the content to less than 10 parts per billion.
  • the process optionally comprises removing or avoiding the production of aminoacetophenone to limit the content to less than 2 parts per billion.
  • the process optionally comprises adding one or more additives to the syrup. These procedures need not be carried out in the same order recited above (for example, the pH adjustment may be performed before adjustment of the dry solids content).
  • the description of the embodiments of the allulose syrup herein applies mutatis mutandis to the process for preparing an allulose syrup.
  • the present invention provides the use of the allulose syrup according to the first aspect in the preparation of a food or beverage product, as well as food or beverage products made using the sweetener syrup.
  • Food or beverage products which may be contemplated in the context of the present invention include baked goods; sweet bakery products (including, but not limited to, rolls, cakes, pies, pastries, and cookies); pre-made sweet bakery mixes for preparing sweet bakery products; pie fillings and other sweet fillings (including, but not limited to, fruit pie fillings and nut pie fillings such as pecan pie filling, as well as fillings for cookies, cakes, pastries, confectionary products and the like, such as fat-based cream fillings); desserts, gelatins and puddings; frozen desserts (including, but not limited to, frozen dairy desserts such as ice cream - including regular ice cream, soft serve ice cream and all other types of ice cream - and frozen non-dairy desserts such as non-dairy ice cream, sorbet and
  • An allulose syrup in accordance with the present invention may be used in combination with one or more other food or beverage ingredients, including any of the food and beverage ingredients known in the art.
  • additional food and beverage ingredients include, but are not limited to, flavorants, colorants, sweeteners other than allulose (including other sugars such as sucrose, fructose, allose, tagatose and other rare sugars, synthetic high intensity sweeteners such as sucralose, acesulfame K, saccharin, aspartame and the like, natural high intensity sweeteners such as Stevia and Monk Fruit Extract sweeteners and the terpene glycosides present therein, and the like), dietary fibers (including soluble dietary fibers such as soluble corn fiber and polydextrose), acidulants, water, and the like.
  • Specific illustrative examples of food and beverage products which may be prepared using an allulose syrup in accordance with the invention include, but are not limited to:
  • a beverage such as a carbonated or non-carbonated beverage or a juice drink comprising allulose syrup and one or more synthetic high intensity sweeteners such as sucralose;
  • a beverage including a beverage concentrate, comprising an allulose syrup, a natural high intensity sweetener (such as a Stevia sweetener), and a dietary fiber (e.g., a soluble dietary fiber, such as a soluble corn fiber), and an acidulant (e.g., citric acid);
  • a beverage concentrate comprising an allulose syrup, a natural high intensity sweetener (such as a Stevia sweetener), and a dietary fiber (e.g., a soluble dietary fiber, such as a soluble corn fiber), and an acidulant (e.g., citric acid);
  • a yogurt such as a Greek yogurt, comprising allulose syrup (which may be free of any artificial sweeteners);
  • a frozen dessert comprising allulose syrup, a dietary fiber (e.g., a soluble dietary fiber, such as a soluble corn fiber), a natural high intensity sweetener (such as a Stevia sweetener and/or a Monk Fruit Extract sweetener), and a food system stabilizer;
  • a dietary fiber e.g., a soluble dietary fiber, such as a soluble corn fiber
  • a natural high intensity sweetener such as a Stevia sweetener and/or a Monk Fruit Extract sweetener
  • a food system stabilizer e.g., a soluble dietary fiber, such as a soluble corn fiber
  • a natural high intensity sweetener such as a Stevia sweetener and/or a Monk Fruit Extract sweetener
  • a cookie such as a chocolate chip cookie, comprising an allulose syrup and a corn starch;
  • a confectionary such as a gummy candy, comprising an allulose syrup and a natural high intensity sweetener (e.g., a Stevia sweetener); and
  • a natural high intensity sweetener e.g., a Stevia sweetener
  • a flavored syrup such as a maple-flavored syrup, comprising an allulose syrup, fructose, and an acidulant (e.g., citric acid).
  • an acidulant e.g., citric acid
  • Example 1 Each sample consisted of 3500 mL of allulose syrup in a 4 quart (4.54 liter) square plastic container. The sampling was carried out at 0 and 2 months.
  • Analytical Samples were analyzed using methods known to those skilled in the art.
  • the allulose composition was determined by standard HPLC methods, such as the Sacch.03 method set forth by the corn refiners association (http://corn.org/wp- content uploads/2009/12/SACCH.03.pdf).
  • DS was measured by refractive index
  • pH was measured at a dilution resulting in less than 40% solids
  • color was analyzed by measuring the absorbance of the syrup at 450nm and subtracting the background at 600nm and dividing the result by the path length of the cuvette.
  • HMF isovaleraldehyde, aminoacetophenone, were analyzed using reverse phase HPLC with UV detection.
  • the HMF content increased in each sample over 2 months (Figure 3).
  • the content of HMF in the sample at 35 °C increased to 180 ppm HMF after 2 months.
  • the content of HMF in the 25 °C and 30 °C samples was lower.
  • Samples of starting material were taken. The pH and DS were measured and recorded. One sub sample of each was taken as is, the next adjusted to pH 3.6, another to pH 4.0 and the final one to pH 4.7 using dilute HCI or sodium carbonate. One subset of starting material was diluted to 71 % DS. Another subset of the pH 4.0 batch had sodium citrate or sodium metabisulfite added. Sealed sample containers were placed into different temperature ovens at 40 °C and 50 °C. Extracts from each of the samples were removed from each oven periodically. Samples were chilled quickly in an ice bath and analyzed for carbohydrate composition, HMF, color and pH.
  • Samples were analyzed to determine their DS, pH, carbohydrate composition, HMF content and color. For pH and color the samples were analyzed at a standard DS.
  • the pH drift data ( Figures 9 and 10) at pH 4.0 matches the stability study of an allulose syrup product which the product pH started at 3.9 and samples were stored at 50°C (comparison in Figure 1 1). Allulose content dropped in all samples following the trend of higher temperature, lower pH and longer time resulting in faster allulose losses ( Figures 12 and 13).
  • the pH 4.0 samples with additives show a similar rate of allulose loss as the pH 4.0 sample with no additive. This may be explained by the similar pH changes observed above and due to very low levels of the additives.
  • Example 3 Crystallization stability Allulose syrups were prepared at 50, 60, 71 , 77, and 85% DS and were equilibrated at 25°C, 15°C and 4°C. These samples were seeded with ⁇ 0.1 % crystalline allulose and crystallization was monitored visually and by change in dry solids of the syrup fraction after 1 month of storage. Results:
  • Microbial stability was assessed at 72% and 77% dry solids content by a challenge study with osmophilic yeasts and molds.
  • Microbial stability was also assessed at 50% and 60% dry solids content by a challenge study with osmophilic yeasts and molds using the same method. At 60%DS, it took allulose syrup 2 months to completely remove viability of osmophilic yeasts and molds, and at 50% DS, viability of yeasts and molds was not removed completely even after 4 months. This suggests that 60% solids is the minimum solids concentration for allulose syrup that can reasonably be considered resistant to spoilage by microbial contamination and more ideally the concentration is 70-77% solids.
  • final product stability has an optimum DS that is fairly narrow for allulose syrup.
  • Lower DS reduces the rate of degradation in all parameters, however a final product DS that is below 60% DS does not maintain good microbial stability.
  • Higher DS results in more rapid degradation and also crystallization. Therefore an optimal DS of 60-80% is required and more preferably a DS of 71 -78% is required for long term stability of allulose syrup and more preferably a DS of 71-73% should have the highest combined allulose content stability, microbial stability and crystalline stability. In cases where microbial stability is the key attribute necessary, 76-78% DS would have the best microbial stability.
  • final product stability is optimized in a narrow range of pH, from 3.5 to 4.5 and more preferably in a pH range from 3.8 to 4.2 in order to optimize the trade-off between carbohydrate stability and color/HMF formation.
  • Lower pH was shown to increase the rate of allulose content loss and HMF formation, while higher pH was shown to result in more rapid formation of color.
  • Example 5 Allulose syrup stability within a narrow pH range and ambient storage temperatures This series of experiments was set up to determine allulose syrup stability within a narrow range of pH and DS at ambient temperature range of 25-35 °C.
  • Additives have an effect on stability. These additives may stabilize the syrup by buffering the pH to help control at pH 4.0 and also to minimize oxidation.
  • Each sample consisted of 1000 mL of syrup in a plastic container. Two gallons of this material were pH adjusted to 4.0 using 1 M sodium carbonate (NaC0 3 ), by slow and careful addition and regular pH measurement at 1 :1 dilution. This material was then split into two separate containers and one was diluted to 71 % DS (1 1.5 lbs 77% DS syrup, plus 0.97 lbs water).
  • HMF HMF increased in all samples. However, one subset of additive samples displayed a substantially smaller amount of HMF increase.
  • the samples with reduced HMF increase were those containing either ascorbate or isoascorbate, displaying less than half the HMF increase of the control samples (Figure 29).
  • Ascorbate and isoascorbate have the ability to control HMF formation, whereas, sodium citrate and sodium acetate showed promise at controlling pH and allulose content changes. Neither MBS nor tocopherol acetate addition resulted in a significant benefit.
  • Example 7 Surface response study of temperature, pH and DS:
  • the acceptable stable storage conditions are further bounded in terms of solids, pH, and storage temperature when color is considered.
  • colorless food ingredients are desired.
  • color of the syrup was analyzed as absorbance at 450nm with background subtracted at 600nm. A change in color of more than 4 is generally considered unacceptable.
  • Change in color for 77% DS allulose syrup were modeled as a response surface after 6 months storage for temperature and pH (Figure 32) we can see that both temperature and pH are critical factors. Temperature must be maintained near or below 25°C and ideally at a pH between 3.7 and 4.2.
  • HMF Hydroxymethylfurfural
  • Figure 34 demonstrates the modeled temperature pH response surface for change in HMF at 77%DS. HMF production is highest at low pH and high temperature and is lowest at high pH and low temperature. Less than 100ppm HMF is generally preferred for food ingredients. Thus, another pH boundary can be placed on allulose syrup: when stored at 25°C, it should be above pH 3.70.
  • a syrup form that is more stable has benefits in that it can be stored for longer time periods and still be saleable, it has broader customer appeal, it can be shipped to geographic locations that require lengthy shipping and holding times. Additionally, improved product stability means that the product as used will retain a higher quality of composition and taste. This is beneficial from a calorie labelling position and final consumer product quality position.

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101695831B1 (ko) 2015-05-15 2017-01-12 주식회사 삼양사 감미질 및 결정화가 개선된 사이코스 혼합당 조성물
RU2727538C1 (ru) 2015-10-02 2020-07-22 Вм. Ригли Джр. Компани Кондитерские изделия, содержащие аллюлозу
MX2018009076A (es) * 2016-03-09 2018-11-09 Cj Cheiljedang Corp Composicion de jarabe que contiene alulosa y alimentos que contienen el mismo.
US20190297931A1 (en) 2016-08-12 2019-10-03 Pfeifer & Langen GmbH & Co. KG Liquid allulose composition
EP3524066A4 (de) 2016-10-06 2020-05-20 CJ CheilJedang Corporation Tomatenketchup mit verbesserter lagerstabilität
US11653684B2 (en) * 2016-10-07 2023-05-23 Cj Cheiljedang Corporation Sweetener composition with improved taste quality comprising allulose and salt and method for improving taste quality of alulose using salt
IL289910B2 (en) 2016-10-28 2023-09-01 Tate And Lyle Ingredients Americas Llc A method for preparing allulose crystals
KR20180066828A (ko) * 2016-12-09 2018-06-19 씨제이제일제당 (주) 고함량의 알룰로스를 함유하는 당류를 포함하는 발효유
AU2017374770B2 (en) 2016-12-13 2022-09-22 Tate & Lyle Solutions Usa Llc Modifying or enhancing a flavor of food and beverage products
EP4256975A3 (de) 2016-12-21 2023-12-20 CJ Cheiljedang Corporation Aminosäuregetränk mit allulose
FR3061415B1 (fr) * 2017-01-05 2021-07-16 Roquette Freres Sirops non cristallisables de d-allulose
FR3061414B1 (fr) 2017-01-05 2021-07-16 Roquette Freres Sirops cristallisables de d-allulose
WO2019004554A1 (ko) * 2017-06-30 2019-01-03 주식회사 삼양사 결정형 기능성 감미료의 제조방법
KR102016701B1 (ko) * 2017-06-30 2019-09-06 주식회사 삼양사 결정형 기능성 감미료의 제조방법
JP6992175B2 (ja) * 2017-10-27 2022-01-13 サムヤン コーポレイション アルロースシロップおよびその製造方法
WO2019088632A2 (ko) * 2017-10-31 2019-05-09 씨제이제일제당 (주) 알룰로스를 포함하는 초코소스 제조용 조성물 및 이의 용도
WO2019088654A2 (ko) * 2017-10-31 2019-05-09 씨제이제일제당 (주) 알룰로스를 포함하는 당류 및 시트러스 추출물을 포함하는 시럽 및 이의 제조방법
KR102246960B1 (ko) * 2017-11-24 2021-04-30 주식회사 삼양사 저칼로리 매운 맛 소스
US11401292B2 (en) * 2018-02-12 2022-08-02 Samyang Corporation Method for producing functional crystalline sweetener
EP3801531B1 (de) * 2018-06-11 2024-09-18 Seattle Gummy Company Gummizusammensetzungen mit niedrigem glykämischem index und verfahren zur herstellung und verwendung davon
CN112292040A (zh) * 2018-06-14 2021-01-29 西雅图咖米公司 低血糖组合物及其制备和使用方法
CA3156624A1 (en) * 2019-10-31 2021-05-06 Jae-Kyung Yang Improved method for manufacturing allulose
KR102332373B1 (ko) * 2019-11-29 2021-11-29 씨제이제일제당 주식회사 알룰로스 이당류를 포함하는 hmf 생성 억제용 조성물
EP4161287A1 (de) 2020-06-05 2023-04-12 Savanna Ingredients GmbH Allulosesirup
MX2023002740A (es) 2020-09-07 2023-04-03 Savanna Ingredients Gmbh Proceso de extrusion para la preparacion de una composicion solida de alulosa.
CN112285228B (zh) * 2020-10-19 2022-05-03 秦皇岛海关技术中心 一种鉴别掺假蜂蜜的方法
EP4000419A1 (de) 2020-11-23 2022-05-25 Savanna Ingredients GmbH Trocknung von allulosekristallen
KR20220096209A (ko) * 2020-12-30 2022-07-07 주식회사 삼양사 안정성이 증가된 알룰로스
TW202406464A (zh) * 2022-06-29 2024-02-16 南韓商三養社股份有限公司 具有絕佳穩定性的阿洛酮糖組成物
WO2024047121A1 (en) 2022-09-01 2024-03-07 Savanna Ingredients Gmbh Process for the preparation of a particulate allulose composition
TW202426055A (zh) * 2022-12-22 2024-07-01 美商玉米製品開發公司 具有改善之穩定性的液體阿洛酮糖糖漿

Family Cites Families (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4263052A (en) 1979-10-12 1981-04-21 American Crystal Sugar Company Production of fructose and useful by-products
US5230742A (en) 1987-02-02 1993-07-27 A. E. Staley Manufacturing Co. Integrated process for producing crystalline fructose and high-fructose, liquid-phase sweetener
US5039346A (en) 1988-03-25 1991-08-13 A. E. Staley Manufacturing Company Fructose syrups and sweetened beverages
JP2876416B2 (ja) 1990-01-31 1999-03-31 株式会社林原生物化学研究所 Ｄ―プシコースの製造方法
ES2126627T3 (es) 1991-08-20 1999-04-01 Staley Mfg Co A E Edulcorante liquido que contiene fructosa y dextrosa.
JP4333094B2 (ja) * 2002-07-16 2009-09-16 不二製油株式会社 濃縮粗大豆オリゴ糖液及びその製造法
KR101191542B1 (ko) 2003-08-25 2012-10-15 카아길, 인코포레이팃드 모나틴을 포함하는 음료 조성물 및 이의 제조 방법
US7435564B2 (en) 2003-09-29 2008-10-14 Instituto Technologico Y De Estudios Superiores De Monterrey Production of invert syrup from sugarcane juice using immobilized invertase
JP4761424B2 (ja) 2004-03-17 2011-08-31 株式会社希少糖生産技術研究所 Ｌ−プシコース結晶、その製造方法および、糖試薬キット
KR100744479B1 (ko) 2005-06-01 2007-08-01 씨제이 주식회사 사이코스 에피머화 효소에 의한 사이코스의 생산 방법
US20070059422A1 (en) * 2005-09-13 2007-03-15 Robbins Gregory C Disaccharide sweetener compounds, process for manufacture, and method of selecting components for dissacaride sweetener compounds based on user specific sweetener applications
EP1956088B1 (de) 2005-11-15 2013-10-23 Hayashibara Co., Ltd. Ketose-3-epimerase, verfahren zur herstellung davon und verwendung davon
US8435587B2 (en) * 2005-11-23 2013-05-07 The Coca-Cola Company High-potency sweetener composition with long-chain primary aliphatic saturated alcohol and compositions sweetened therewith
EP1965667A2 (de) * 2005-11-23 2008-09-10 The Coca-Cola Company Synthetische süssmittelzusammensetzungen mit verbessertem zeitverlaufsprofil und/oder geschmacksprofil, verfahren zu ihrer formulierung und ihre verwendungen
US8057840B2 (en) 2006-01-25 2011-11-15 Tate & Lyle Ingredients Americas Llc Food products comprising a slowly digestible or digestion resistant carbohydrate composition
EP2090180A4 (de) * 2006-11-10 2013-08-21 Matsutani Kagaku Kogyo Kk Süssstoff enthaltende d-psicose, und nahrungsmittel und getränke, die durch verwendung desselben erhalten werden
KR100832339B1 (ko) 2006-12-11 2008-05-26 솔젠트 (주) 과당을 사이코스로 전환하는 신규한 시노리조비움 속균주와 이를 이용한 사이코스 생산법
JP4931741B2 (ja) * 2007-09-04 2012-05-16 アサマ化成株式会社 糖類組成物及びその製造方法
KR101523701B1 (ko) 2008-03-12 2015-06-01 주식회사 케이엠더블유 무선통신기기의 함체장치
WO2010113785A1 (ja) 2009-03-30 2010-10-07 松谷化学工業株式会社 目的とするヘキソースを所定量含む原料糖とは異なる糖組成の糖組成物の製造方法および製造された糖組成物の用途
KR20110035805A (ko) 2009-09-30 2011-04-06 씨제이제일제당 (주) 사이코스-에피머화 효소의 고정화 및 이를 이용한 사이코스의 제조방법
KR101159934B1 (ko) 2009-12-30 2012-06-25 주식회사 삼양제넥스 결정 석출 또는 백탁 현상이 발생하지 않는 안정화된 프락토올리고당 시럽 조성물
KR101189640B1 (ko) * 2010-03-26 2012-10-12 씨제이제일제당 (주) Ｄ-사이코스 결정을 제조하는 방법
JP2011200201A (ja) 2010-03-26 2011-10-13 Kishoto Seisan Gijutsu Kenkyusho:Kk 複数の糖からなる複合体結晶糖質を含有する糖ペーストその製造方法およびその用途
JP2011205913A (ja) 2010-03-29 2011-10-20 Kishoto Seisan Gijutsu Kenkyusho:Kk 機能性異性化糖の複合体結晶糖質およびその製造方法
JP5859191B2 (ja) * 2010-09-29 2016-02-10 松谷化学工業株式会社 高甘味度甘味料に対する呈味改良組成物およびその応用
EP3556763A1 (de) * 2010-12-13 2019-10-23 Cargill, Incorporated Glykosidmischungen
JP5922880B2 (ja) 2011-04-28 2016-05-24 松谷化学工業株式会社 結晶糖質、その製造方法ならびに用途
ES2657021T3 (es) 2011-09-15 2018-03-01 Cj Cheiljedang Corporation Composición edulcorante para aliviar la diabetes, que contiene un ingrediente de digestión lenta
JP6099870B2 (ja) * 2012-01-06 2017-03-22 松谷化学工業株式会社 スクロースとｄ−プシコースを含む新規甘味料
JP6041420B2 (ja) * 2012-02-29 2016-12-07 三井製糖株式会社 糖液及びその製造方法
JP6349262B2 (ja) 2013-01-31 2018-06-27 国立大学法人 香川大学 血糖値の上昇抑制効果を有するこんにゃく加工飲食品
US20140322389A1 (en) 2013-03-14 2014-10-30 Indra Prakash Beverages containing rare sugars
GB201309077D0 (en) 2013-03-15 2013-07-03 Tate & Lyle Ingredients Improved sweetener
WO2014152083A1 (en) 2013-03-15 2014-09-25 The Procter & Gamble Company Personal care article comprising dissolvable fibers
GB201309079D0 (en) * 2013-03-15 2013-07-03 Tate & Lyle Ingredients Improved sweetner
GB201309076D0 (en) * 2013-03-15 2013-07-03 Tate & Lyle Ingredients Improved sweetener
KR102272145B1 (ko) 2013-04-08 2021-07-01 마쓰다니가가꾸고오교가부시끼가이샤 음식물의 짠맛 증강 방법 및 상기 방법에 의해 얻어지는 음식물 및 짠맛 증강제
CN103288887B (zh) * 2013-06-04 2016-01-27 北京大学 一种由醛糖制备酮糖的方法
JP6212316B2 (ja) 2013-07-24 2017-10-11 松谷化学工業株式会社 飲食物の異味異臭をマスキングする方法及び該方法により得られる飲食物
MX2016006684A (es) 2013-11-22 2016-09-08 Tate & Lyle Ingredients Americas Llc Productos alimenticios y bebidas que contienen alulosa (psicosa).
AU2013408190A1 (en) 2013-12-20 2016-07-07 Roquette Freres Protein food product comprising D-allulose
BR112017017941B1 (pt) 2015-02-24 2022-09-27 Tate & Lyle Ingredients Americas Llc Xarope de alulose, seu processo de preparação, uso do mesmo, e produto alimentício ou de bebida

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4042873A1 (de) 2015-02-24 2022-08-17 Tate & Lyle Solutions USA LLC Allulosesirup

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KR20210096688A (ko) 2021-08-05
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TW201639863A (zh) 2016-11-16
BR112017017941B1 (pt) 2022-09-27
US20230248038A1 (en) 2023-08-10
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EP3261455B8 (de) 2022-02-16
AU2020203857A1 (en) 2020-07-02
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